623-66-5Relevant academic research and scientific papers
One-pot electrochemical synthesis of acid anhydrides from alcohols
Kashparova,Papina,Kashparov,Zhukova, I. Yu.,Ilchibaeva,Kagan, E. Sh.
, p. 2733 - 2735 (2017/12/26)
One-pot indirect electrochemical oxidation of alcohols in the methylene chloride–aqueous solution of sodium hydrocarbonate two-phase system in the presence of potassium iodide, 4-acetylamino-2,2,6,6-tetramethylpiperidin-1-oxyl, and 2,6-lutidine results in
One for Many: A Universal Reagent for Acylation Processes
Moon, Hyun Kyung,Sung, Gi Hyeon,Kim, Bo Ram,Park, Jong Keun,Yoon, Yong-Jin,Yoon, Hyo Jae
supporting information, p. 1725 - 1730 (2016/06/09)
This work describes acylation reactions facilitated by a type of heterocycle-based acyl transfer agent, 2-acyloxypyridazinone. Reactions of 2-acyloxypyridazinone with carboxylic acids yield mixed carbonic anhydride intermediates, which are reactive and could be coupled with a wide range of substrates including acids, amines, alcohols, and thiols. The wide substrate scope, ease of operation (no additive or catalyst), storage and handling stability, and atom-efficiency from recycling the heterocycle carrier make the reported acylating agent attractive for acylation-based coupling reactions.
Elucidation of the topography of the thapsigargin binding site in the sarco-endoplasmic calcium ATPase
Skytte, Dorthe Mondrup,Moller, Jesper Vuust,Liu, Huizhen,Nielsen, Helle stergren,Svenningsen, Louise Elsa,Jensen, Christina Mernoe,Olsen, Carl Erik,Christensen, Soren Brogger
experimental part, p. 5634 - 5646 (2010/09/14)
Removal of each of the acyl groups of thapsigargin at O-3, O-8 and O-10 significant reduces the affinity of the inhibitors to the SERCA1a pump. Replacement of the acyl groups at O-3 and O-10 with flexible residues could be performed with only a minor decrease of the affinity, whereas introduction of voluminous stiff residues caused dramatic reduction of the affinity. The results can be rationalized on the basis of the interactions of thapsigargin with the SERCA1a pump as revealed from 3D X-ray structural models of thapsigargin bound to the SERCA1a. In conclusion the results confirm and elaborate the previously suggested pharmocophore model of thapsigargin.
Effective esterification of carboxylic acids using (6-oxo-6H-pyridazin-1-yl)phosphoric acid diethyl ester as novel coupling agents
Won, Ju-Eun,Kim, Ho-Kyun,Kim, Jeum-Jong,Yim, Heong-Seup,Kim, Min-Jung,Kang, Seung-Beom,Chung, Hyun-A.,Lee, Sang-Gyeong,Yoon, Yong-Jin
, p. 12720 - 12730 (2008/03/14)
(6-Oxo-6H-pyridazin-1-yl)phosphoric acid diethyl esters (3) are efficient and selective coupling agents for equimolar esterification of carboxylic acids and alcohols. Esterification of aliphatic and aromatic carboxylic acids with aliphatic and aromatic alcohols using 3 afforded the corresponding esters chemoselectively in good to excellent yield.
Identification of a tunable site in bryostatin analogs: C20 bryologs through late stage diversification
Wender, Paul A.,Baryza, Jeremy L.
, p. 1177 - 1180 (2007/10/03)
The C20 region of our bryostatin analogs was identified as a nonpharmacophoric site that could be varied to tune analogs for function and physical properties without significantly affecting their binding affinity for PKC. The use of this site in a late-stage diversification strategy has enabled the facile synthesis of a variety of new C20 analogs, all of which retain nanomolar affinity for PKC, in agreement with our pharmacophore hypothesis.
γ,δ- and δ,ε-unsaturated aldehydes from γ- and δ-lactones in one step: Preliminary communication
Giersch, Wolfgang,Naef, Ferdinand
, p. 1697 - 1703 (2007/10/03)
A one-step transformation of δ- and δ-(spiro)lactones into δ,δ- and δ,ε-unsaturated aldehydes with an excess of formic acid in the vapor phase over a supported manganese catalyst is described for the first time. The scope and limitations of this new reaction are shown with different lactones as substrate, and a mechanistic rationale is proposed.
Direct hydrogenation of carboxylic acids to corresponding aldehydes catalyzed by palladium complexes
Nagayama,Shimizu,Yamamoto
, p. 1803 - 1815 (2007/10/03)
A variety of carboxylic acids can be directly hydrogenated into the corresponding aldehydes in high yields by using homogeneous catalysts such as [Pd(PPh3)4] or combination of Pd(OAc)2 with tertiary phosphines in the presence of an excess amount of 2,2-dimethylpropionic anhydride (pivalic anhydride). As a typical example, octanoic acid can be convened into octanal in 99% yield in 3 h at 80 °C under 3.0 MPa of H2 in acetone in the presence of pivalic anhydride and a catalyst system composed of Pd(OAc)2 + 5P(p-tol)3. Such hydrogenation is widely applicable to various aliphatic, aromatic, and heterocyclic carboxylic acids as well as to di- and tribasic carboxylic acids. The process allows the presence of other functional groups such as ketonic carbonyl, nitrile, and ester groups and even internal C=C bonds. Heterogeneous palladium catalyst such as palladium on carbon also showed some catalytic activities.
A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetonitrile and triphenylphosphine
Kim,Jang
, p. 395 - 399 (2007/10/03)
Various carboxylic acids are converted into the corresponding carboxylic acid anhydrides treated with trichloroacetonitrile and triphenylphosphine in the presence of triethylamine at room temperature.
Cobalt(II)-Catalyzed Reaction of Aldehydes with Acetic Anhydride under an Oxygen Atmosphere: Scope and Mechanism
Bhatia, Beena,Punniyamurthy, T.,Iqbal, Javed
, p. 5518 - 5523 (2007/10/02)
The reaction of aldehydes with acetic anhydride in the presence of catalytic cobalt(II) chloride under an oxygen atmosphere at ambient temperature is dependent upon the reaction medium.Aliphatic aldehydes react in acetonitrile to give 1,2-diones whereas the aromatic aldehydes are acylated to yield the corresponding acylals.On the other hand, carboxylic acids are obtained from aliphatic and aromatic aldehydes by conducting the reaction in dichloroethane or benzene.Cobalt(II) chloride in acetonitrile catalyzes the conversion of aliphatic aldehydes to the correspondinganhydrides in the absence of acetic anhydride whereas aromatic aldehydes remain largely unaffected under these conditions.A preliminary mechanistic study in three different solvents (i.e. acetonitrile, dichloroethane, and DMF) has revealed that in acetonitrile and in the presence of acetic anhydride, aliphatic aldehydes behave differently than aromatic aldehydes.Some trapping experiments using methyl acrylate and stilbene have been conducted to demonstrate the occurence of an acyl cobalt and peroxyacyl cobalt intermediate during these reactions.
A CONVENIENT PREPARATION OF CARBOXYLIC ACID ANHYDRIDES USING A "SUPPORTED" PHOSPHORUS PENTOXIDE REAGENT
Burton, Stephanie G.,Kaye, Perry T.
, p. 3331 - 3336 (2007/10/02)
Treatment of carboxylic acids with a "supported" phosphorus pentoxide reagent provides a convenient route to the corresponding anhydrides.
